Synthesis of creosyl palmitate

Palmitic acid (1.40 g, 5.46 mmol), creosol (0.76 g, 5.50 mmol), EDC.HCL (1.24 g, 6.47 mmol) and DMAP (67.1 mg, 0.550 mmol) were added to acetonitrile (25 mL). The mixture was refluxed for two hours, with TLC being performed in 20 minute intervals on a sample of the reaction mixture and on creosol. The reaction was stopped when the creosol spot in the reaction mixture no longer showed prominently on the TLC plate, and the mixture was allowed to cool to room temperature. Hexane (20 mL) was added to the mixture, which was washed with 1 M HCl (2 x 20 mL), 10 wt% NaHCO3 (2 x 20 mL), water (20 mL) and saturated NaCl (2 x 20 mL). The mixture was then dried with anhydrous MgSO4 and filtered under gravity. The solvent was removed from the resulting solution by rotary evaporation at 40 °C to afford creosyl palmitate as white crystals (0.45 g, 1.20 mmol, 21.7 %). M.p. 43.4-45.2 °C. FT-IR ν (cm−1) = 1750 (C=O), 2910 (C-H). Mass spec m/z = 137.7, 238.6, 270.7, 376.4 (M+). 1H NMR (400 MHz, CHLOROFORM-D) δ 7.25 (d, J = 8.0 Hz, 1H), 7.13 (d, J = 1.9 Hz, 1H), 7.09 (dd, J = 8.0, 1.9 Hz, 1H), 4.16 (s, 3H), 2.92 (t, J = 7.5 Hz, 2H), 2.70 (s, 3H), 2.12 (tt, J = 7.8, 7.4 Hz, 2H), 1.83 – 1.57 (m, 24H), 1.25 (t, J = 6.9 Hz, 3H).